Dispersion of silver halide developing agent with surface active polymers of maleic acid half esters

ABSTRACT

A dispersion comprising an hydrophilic organic colloid, fine droplets of silver halide developing agent dissolved in a substantially water-insoluble solvent, and a surface active polymer containing therein recurring units represented by the formula (I):   WHEREIN R is a hydrocarbon chain or fluorine substituted hydrocarbon chain containing 4 to 22 carbon atoms, or an aryl group; n is 0 or an integer of 1 to 40; and M is a hydrogen atom or a cation.

Uited States atet 11 1 Miyakawa et al.

1 51 Dec. 30, 1975 [54] DISPERSION OF SILVER HALIDE DEVELOPING AGENT WITH SURFACE ACTIVE POLYMERS OF MALEIC ACID HALF ESTERS [75] Inventors: Masami Miyakawa; Masakazu Yoneyama; Nobuo Yamamoto, all of Minami-ashigara, Japan [73] Assignee: Fuji Photo Film Co., Ltd.,

Minami-ashigara, Japan [22] Filed: July 26, 1974 21 Appl. No.: 492,312

[30] Foreign Application Priority Data July 26, 1973 Japan 48-84438 52 us. (:1 96/66 R; 96/3; 96/29 D; 96/76 R; 96/77; 96/95; 96/97; 96/114.5 51 1111. (11. G03C 5 30; GO3C 1/48; G03C 1/40;

3,5l8,088 6/1970 Dunn et al. 96/76 R 3,589,902 6/1971 Himmelmann et al 96/66 R 3,647,437 3/1972 3,785,824 1/1974 Fisch 96/66.1

Primary Examiner-David Klein Assistant ExaminerRichard L. Schilling Attorney, Agent, or FirmSughrue, Rothwell, Mion, Zinn & Macpeak [57] ABSTRACT A dispersion comprising an hydrophilic organic colloid, fine droplets of silver halide developing agent dissolved in a substantially water-insoluble solvent, and a surface active polymer containing therein recurring units represented by the formula (I):

MOO boocmcu og iz wherein R is a hydrocarbon chain or fluorine substituted hydrocarbon chain containing 4 to 22 carbon atoms, or an aryl group; n is 0 or an integer of 1 to 40; and M is a hydrogen atom or a cation.

54 Claims, No Drawings AGENT WITH SURFACE ACTIVE POLYMERS OF MALEIC ACID HALF ESTERS BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a dispersion of a silver halide developing agentin a hydrophilic organic colloid, which is contained in a color photographic element. The dispersion is applicable particularly to the diffusion transfer color process.

2. Description of the Prior Art One of the diffusion transfer color processes is the dye developer process, which is described in British Pat. No. 804,971, US. Pat. Nos. 3,415,644, 3,415,645, 3,415,646, 3,594,164 and 3,594,165, and Japanese Patent Publication No. 16356/1971, etc. In this process, a photographic element comprising a silver halide emulsion layer and a layer containing a dye developer which is diffusible in an alkaline solution (a dye which acts to develop silver halide), is exposed to form a latent image in the silver halide and is processed with an alkaline composition which can permeate the silver halide emulsion layer and the layer containing the dye developer, whereby the latent image is developed with the dye developer which is diffused with the alkali and at the same time, an oxidation product of the dye developer is produced and is rendered essentially non-diffusible in the hydrophilic colloidal layer.

It is apparent that the non-diffusion of the oxidized dye developer is partially due to the reduced solubility thereof in the alkaline composition and that the diffusion of the oxidized dye developer in the hydrophilic colloidal layer is prevented by the hardening action of the oxidized dye developer on the hydrophilic colloid.

The unoxidized dye developer is partially or entirely transferred to an image receiving element overlaid thereon through diffusion, thereby providing a positive dye image.

Where an element is used which contains silver halide emulsion layers having different sensitivity and dye developers capable of providing color images corresponding to the color sensitivity of the silver halide emulsion layers, after exposure followed by processing with an alkaline composition, the remaining dye developer which is not consumed at the time of the development of the silver halide emulsions is transferred to a receiving element, whereby a multi-color positive image is obtained.

For instance, a dye former which provides a cyan transfer image is present in a red sensitive emulsion layer or in a colloidal layer adjacent the emulsion layer.

.A dye former which provides a magenta transfer image is present in a green sensitive emulsion layer or in a colloidal layer adjacent the emulsion layer. A dye former which provides a yellow transfer image is present in a blue sensitive layer or in a colloidal layer adjacent the emulsion layer. A photosensitive element comprising the above described red sensitive layer, green sensitive layer, and blue sensitive layer is exposed and treated with an alkaline composition, whereby a multicolor positive image is transferred to a receiving element overlaid on the photosensitive element. In this case, it is preferred that auxiliary developing agents are used to facilitate the development of the silver halide and the fixing of the dyes in the photosensitive element. The auxiliary developing agents are colorless, waterinsoluble, and soluble and diffusible in an alkaline solution through a hydrophilic organic layer such as gelatin.

It is necessary that the colloidal particles of the dye developer or the auxiliary developing agent be as small as possible and thus that the surface thereof be as large as possible. The reason is that the dissolution, diffusion and permeation of the dye developer or the auxiliary developing agent in the alkaline solution at the developing step is effected through the interface between the dispersed particles and the gelatin gel.

Mechanical techniques as well as surface chemical techniques are emmployed to prepare the above described fine particle dispersion. As the surface chemical techniques, surface active agents are generally used as an emulsifying agent. The emulsifying agent is effective in not only preparing fine particles, but providing storage stability for the particles for a long period of time. Preferably, the dispersion is stored after cool-setting or removing the solvent of the developing agent by evaporation or washing for the purpose of preventing the recombination of colloidal particles and preventing the crystal growth of the developing agent. With this procedure, however, it is difficult to store the dispersion for a long period of time while maintaining a fine particle size and without causing a crystalization of the developing agent. It is particularly difficult to eliminate the crystalization in the developing agent dispersion layer after the layer is coated and dried.

The dye developer should be non-diffusible and should not form coarse crystal grains in the photosensitive element prior to the alkaline solution processing and during the alkaline solution processing and it should be diffusible in the hydrophilic colloid. The introduction of various oleophilic substitutents in the dye developer will render the dye developer easily soluble in a water-insoluble solvent for dispersion, but diffusion of the resulting dye developer is difficult at the processing stage. Thus, it is generally impossible to introduce a highly oleophilic substituent. In general, therefore, the dye developer has a low degree of disperability in the water-insoluble solvent and coarse crystal grains tend to form in a dispersion thereof in an aqueous gelatin solution.

Thus, it is quite difficult to prepare an emulsion which is free from aggregation and crystalization with time, by emulsifying and dispersing the dye developer which is not suitable for emulsification and dispersion from a chemical structure standpoint, in a hydrophilic organic colloidal solution in the form of fine colloidal particles (the diameter of which desirably is below about 0.5 microns). It is very important to find effective emulsifying and dispersing agents. Where an emulsifying agent for an oil-soluble coupler, which is often used for conventional color photographic photosensitive element, is applied to the emulsification and dispersion of a dye developing agent, the crystalization and growth of the grains often occurs as is indicated in the Examples as described hereinafter.

In emulsifying and dispersing using a combination of gelatin and a surface active agent, difficult problems are caused by the foaming properties of the emulsifying agent, e.g., the emulsifying efficiency is lowered. Particularly, the coating of the emulsion and the photographic emulsion at the subsequent step becomes difficult. That is, a large amount of bubbles are incorporated in the liquid through vigorous stirring and the shearing force of an emulsifying machine is considerably reduced by the cushioning effect of the bubbles and porated in the emulsion at the emulsifying stage often remain in the coating liquid, resulting in the formation of pin-holes when coated. In. general, when the emulsifying agent used in emulsifying and dispersing thedye developer agent has asurface activityiwhich is .too high,

such is not desirablein that the above mentioned crystaliz ation and formation of air bubbles result. On the other hand, when the emulsifying agent has excellent emulsifying and dispersing capability, but has low surface activity and low spreadability, the coating of the emulsion becomes difficult. ,"Thus, the techniques to sufficiently finely disperse 'th'edyedeveloper, to prevent the dye developer from becoming coarse-grained, and to provide the dye developer with high reactivity and diffusibility with the alka- 'line'solutii'yn for developing silver halide in the adjacent layer, are quite specific and conventionally used emul- 'si fyingand dispersing techniques can not be applied to achiev' 'ethese results.

. ."SUMMARY OF THE INVENTION ltis an ob jec t of the present invention .to provide a dispersion wherein a compound capable of acting as a reductant for an exposed silver halide, such as a dye developer, and/or an auxiliary developing agent (which developing agen tf or developing agents are herein referred to-as a silver halidedeveloping agent), is contained in a hydrophilic organic colloid in the vform of fine colloidal particles without adversely affecting the photographic properties.

It is another object of the present invention to provide a dispersion wherein the silver halide developing agent emulsified and dispersed is prevented from aggregationand crystal separation with time.

It is a further object of the present invention to provide a dispersion suitable for providing an emulsion layer in which crystal separation of the dye developer is prevented. I

These objects can be attained in a system comprising a hydrophilic organic colloidcontaining fine particles of a silver halide developing agent dissolved in a substantially water-insoluble solvent and at least one surface active polymer containing the recurring unit represented by the general formula (I):

wherein R is a hydrocarbon chain or fluorine substituted hydrocarbon chain containing 4 to 22 carbon atoms, or an aryl group; n is O or an integer of l to 40; and M is a hydrogenatom or a cation.

DETAILED DESCRIPTION OF INVENTION The hydrocarbon chain orfluorinei substituted hydro carbon chain can be .a straight. or branched chain, or

4 can contain unsaturated bonds provided that it contains 4 to 22 carbon atoms. Suitable'examples of hydrocarbon chainshaving 4 to 22 carbon atoms include n-butyl, sec-butyl-,- iso-butyl, tert-butyl, n-amyl, isoamyl, neopentyl, tert-amyl, n-hexyl, pinacolyl, n-heptyl, pentamethylethyl, n-octyl, iso-octyl, n-nonyl, ndecyl, n-dodecyl, n-tetradecyl, n-hexadecyl, n-pentadecyl, n-eicosyl, etc., suitable examples of fluorine substituted hydrocarbon chains, having 4 to 22 carbon atoms include 3,3,4,4-tetrafluorobutyl, dodecafluorononyl, tetracosafluorotridecyl, octacosafluoropentadecyl, perfluorooctyl, perfluorohaptadecyl, etc., and examples of hydrocarbon chains containing unsaturation include crotyl, l-methyl-Z-propenyl, l-di-methyl-3- butenyl, 3-butenyl, lO-undecenyl,- l-methyl-2-butenyl, cis-9=oc'tadecenyl, 4-pentenyl, 2,4-pentadienyl, 1- m'ethyl-3-butenyl, 2,4-hexadienyl, l-vinyl-2-butyl, etc. Representative examples of aryl groups are unsubstituted aryl groups such as phenyl and 'naphthyl, and substituted aryl groups containing substituents such as alkyl, e.g., dodecyl; alkylamino, e.g., oleylamino; alkoxycarbonyl, e.g., octoxycarbonyl; acyloxy, e.g., octanoyloxy; acylamino, e.g., octanoylamino; alkylcarbamyl, eg, octylcarbamoyl; and the like. These aryl groups suitably contain up to 22 carbon atoms, e.g., 6

to 22 carbon atoms.

Representative examples of M are hydrogen ion, and cations, e.g alkali metal ions such as sodium ion, potassium ion and the like, ammonium ion, and trialkyl ammonium ion such as trimethyl ammonium ion, etc. The surface active polymers containing the recurring unit represented by the above described formula include those copolymers produced from maleic anhydride or maleic acid half ester salts, and monomers copolymerizable therewith, such as ethylene,- styrene, methyl vinyl ether, methyl methacrylate, ethyl acrylate, acrylonitrile, acrylamide, vinyl acetate, vinyl chloride, and the like. Thepolymer produced from maleic anhydride must be cleaved by alcohol decomposition. However, the present invention is not limited tothe above described polymers only and all the polymers containing the above recurring unit can be used in the present invention. Polymers are suitable to achieve the objects of thisinvention as long as the amount of the repeating unit of the formula (I) is at least 10 percent by weight.

,A preferred embodiment of these copolymers can be represented by the following general formulae (II) and (III) (ll) MOOC COO-(CH,CH,O-)R

and

wherein R n and are as defined above and the molar ratio of x to y ranges from 3:1 to 9: l Copolymers of the general formula (ll). above are particularly preferred.

Representative specific examples of these polymers are as follows. Compound 1 (molar ratio ofx to y: 1:1) Compound 2 (molar ratio of x to y: 1:1)

Compound 3 (molar ratio of xto y: 1:1) Compound 4 (molar ratio of x to y:'L1:1) Compound 5 r (molar ratio ofx to 1:1) Compound 7 (molar ratio ofx to y: 2:1)

Compound 8 (molar ratio of x to y: 1:1) Compound 9 (molar ratio of x to y: 3:1) Compound 10 (molar ratio of x to y: 2:1) Compound 11 (molar ratio of x to y: 1:1) Compound 12 v(molar ratio of x to y: 1:1)

Compound 1 3 (molar ratio of x to y: 1:1) Compound 14 (molar ratio of x to 1:1)

produced 'by dissolving the product prepared as described above in an aqueous alkali by heating. On the other hand, the copolymers can be easily produced in a conventional manner, e.g.,.*as disclosed in US. Pat; Nos. 3,549,605; 3,448,708; and 3,525,620. The molecrange from about 250 to 100,000. Preferably the molecular weight of the copolymers ranges from about 1,000 to- 20,000. The amount of the surface active polymer added varies depending on the kind of silver halide developing agent and the solvent, and the amount of the silver halide developing agent and solvent, and the amount can range up to about 200% by weight. Preferably it-is.in the range of about 0.5 to 50% by weight based on the weight of the silver halide developing agent. The surface active polymer can be used alone or in combination with surface active agents with anionic and nonionic surface active agents being preferred. Suitable surface active agents include the following examples. Aliphatic acid salts:

sodium myristate, sodium palmitate, sodium stearate, sodium oleate, sodium linoleate, sodium laurate, sodium caprate, potassium. laurate, potassium stearate,

.etc.,

Alkylsulfates:

sodium octadecylsulfate, sodium decyls'ulfate, sodium dodecylsulfate, sodium tetradecylsulfate, sodium hexadecylsulfate, potassium decylsulfate,ppotassium oleylsulfate, ect., Alkylphosphates: a,

sodium octylphosphate, sodium dioctylphospha't'ee sodium nonylphosphate, sodium decylophosphate,'potassium undecylphosphate, potassium dodecylphosphate, potassium pentadecylphosphate. etc., Alkylsulfonateszsodium dodecylsulfonate, sodium hexadecanesulfonate, sodium octadecanesulfonate, etc., Alkylarylsulfonates:

potassium octylbenzenesulfonate, sodiumnonylbenzenesulfonate, sodium decylbenzenesulfonate, sodium undecylsulfonate, sodium dodecylbenzenesulfonate, sodium tridecylbenzenesulfonate, sodium dibutylnaphthalenesulfonate, sodium decylnaphthalenesulfonate,

sodium octylnaphthalenesulfonate, potassium pentyl- 60 naphthalenesulfonate, etc., R l I Frmaldehyde -condensates with alkylnaphtl'ialenesulfonates:

sodium formaldehyde-condensate with naphthalenesulfonate, sodium formaldehyde-condensate butylnaphthalenesulfonate, etc.,

ular weight of the copolymers is not limited and can 8 Alkyldiphenylether sulfonates:

sodium nonyldiphenylether sulfonate, sodium decyldiphenylether sulfonate, sodium dodecyldiphenylether disulfonate, etc. 5 Dialkylsulfosuccinates:

sodium dihexylsulfosuccinate, sodium dioctylsulfosuccinate, sodium dinonylsulfosuccinate, etc., Polyoxyethylene alkyl ethers and the sulfuric ester salts thereof:

polyoxyethylene lauryl ether, polyoxyethylene oleyl ether, sodium polyoxyethylene lauryl ether sulfate,

sodium polyoxethylene oleyl ether sulfate, po1yoxyeth.-.

ylene dodecyl ether, polyoxyethylene tetradecyl ether, polyoxyethylene hexadecyl ether, polyoxyethylene octadecyl ether, etc., Polyoxyethylene alkylaryl ethers and the sulfuric ester salts thereof: I

sodium polyoxyethylene nonylphenyl etherrsulfate, polyoxyethylene nonylphenyl ether, sodium ethyl dibutylphenyl ether sulfate, etc., 1 Polyoxyethylene alkyl esters and the sulfuric ester salts thereof:

' polyoxethylene stearic acid ester, polyoxyethylene palmitic acid ester, sodium polyoxyethylene stearic acid ester sulflate, sodium polyoxyethylene lauric acid ester sulfate, sodium polyoxyethylene capric acid ester sulfate, sodium polyoxyethylene myristic acid ester sulfate, etc., Sorbitan alkyl esters: sorbitan monolauric acid ester, sorbitan 'monop'almitic acid ester, sorbitan monostearic acid ester, sorbitan tristearic acid ester, sorbitan monooleic acid ester, sodium sorbitan trioleate, etc., Polyoxyethylene sorbitan alkyl esters:

polyoxyethylene sorbitan monolauric acid ester, polyoxyethylene sorbitan inonostearic acid ester, polyoxyethylene monooleic acid ester, polyoxyethylene sorbitan monopalmitic acid ester, polyoxyethylene trioleic acid ester, etc.,

4 Others:

polyoxyethylene mannitan monolauric acid ester, styrenemaleic acid half ester copolymer, etc. F

The dye developers as used in the present invention are dye developers, which'are described in US. Pat.

Nos. 2,983,605, 2,983,606, 2,992,106, ,3,047,386,

3,482,972, and 3,563,739; Australian Pat. No. 220,279; German PaLNo. 1,036,640; British Pat. Nos. 804,971, 804,973, 804,974, and 804,975 Belgian Pat.

Nos. 554,935 and 568,344; Canadian Pat. Nos. 579,038 and 577,021; French Pat. No. 1,168,292; etc.

The dye developers are characterized in that they are slightly soluble in water and non-diffusible under acidic and neutral conditions and they are diffusible under alkaline condition.

Representative examples of the dye developers include the-following compounds.

1 -Phenyl-3-N-n-hexylcarbamoy1-4-p-(2- hydroquinonylethyl)-phenylazo-5-pyrazolone 2-p-(2-1-1ydroquinonylethy1)-phenylazo-4-isopropoxy- 1 -naphthol pp y y- 15 16 CH OH droquinone, 2-dimethylaminomethyltoluhydroquinone, 2-cyclohexylhydroquinone, sec-butylhydroqui- OH OH NH CH CH CH none, 2,S-dichlorohydroquinone, 2,5-diisopropylhy- 2 2 I droquinone, 2,5-diiodohydroquinone, 3-chlorotoluhy- 5 droquinone, tetrachlorohydroquinone, 2,5-diphenylhy- I droquinone, 2,5-diresorcylhydroquinone, 2,5-dioctyl- I OH hydroqu none, dodecylhydroquinone, 4-methoxycatechol. 4-isopropoxycatechol, 3-isopropylcatechol, 4- I I OH phenylcatechol, 3,6-dimethylcatechol, 1,2-dihydroxy- H OH I 5,8-methano-5,6,7,9-tetrahydronaphthalene, etc.

NH C CH CH These silver halide developing agents are generally I 2 I dissolved in a high boiling solvent (e.g., above 150C) CH and, if desired, an auxiliary solvent, and dispersed in an 5 about 1 to by weight, preferably about 10% by 011 weight, aqueous solution of a hydrophilic organic colloid such as gelatin, in the form of fine colloidal partil4'bls[(Y'HydrOqumOHyI'a'methYI)' cles, having a particle size of less than about 1 [1,, prefpropylamino]- 5,8,9,lO-tetrahydroxyanthracene erably less than 0.5 [1,. With the high molecular weight l-(o-Carboxyphenyl)-3-phenyl-4-[p-(2 ,5 -trisurfactant of this invention aparticle size of about 0.3 fluoroacetoxy-B-phenylethyl)phenylazo]-5- 20 M can be used hydroxypyrazole lactone In addition to the gelatin described-above, the follow- OH ing can be used as the hydrophilic organic colloid: I phthalated gelatin, polyvinyl alcohol, polyvinyl pyrrol- NHCO-C -C-N=N- CH CH idone,polyacrylamide, sodium polyacrylate,polyvinyl- II I 2-methylidazole, acrylamide/ l -vinyl-2- N C methylimidazole copolymers, acrylamide/imidazole. w I copolymers, acrylamide/l-vinyl-2-methylimidazo'le/a- OH or lic acid co ol mers, nitrocarbox methylcellulose, y P y Y N-vin l rrolidone-acr lic acid copol mers, N-vinyl- /C YPY y y I pyrrolidone-acrylic acid-methyl acrylate copolymers, vinylphthalimideacrylic acid copolymers, cellulose acetate hydrogen phthalate, poly-N-methylmethacrylayp y -p y y -[pmide, dimethylaminoethylmethacrylate-acrylic acid (fi-hy q y y )p y ly copolymers, dimethylaminoethylmethacrylate-acrylic ypyrazole lactone I I acid-butyl acrylate copolymers, N,-N-diethylacrylall y y yyroyloxy-phenylmemide-acrylamide copolymers, poly-N-methylacrylathyl)]-phenylazo}-B-(2 -benzofuranyl)-B- mide copolymers, N-methylacrylamide-N-hydroxyme- .butyroyloxyacrylonitrile thylacrylamide copolymers, poly-N-ethylacrylamide, 2-[m-(2',5-Butyroyloxy-phenylmethyl)phenylaz01- 40 methylvinylketoneacrylamide copolymers, N-vinylpyr- 3-butyroyloxybenzothiophene rolidone-methacrolein copolymers, and the like. If dea-[p-(2,5-Butyroyloxy-B-phenylethyl)-phenylaz0l-B- sired, they can be used in combination with each other. (2'-benzofuranyl)-B-butyroyloxy-acetonitrile Furthermore, they can be used in combination with OH OCOCOOC H N=N- -CH CH IDCR OCOCOOC I-I 2-[p-(2,5-Ethoxyoxaloxyphenethyl)phenylazo]- synthetic polymers such as cellulose acetate and the 4-methoxy-l-naphthol like. The high boiling solvent is an organic solvent Suitable auxiliary developing agents are described in which is used for dispersing the silver halide developing British Pat. No. 1,243,539, US. Pat. No. 3,253,915, agent in the hydrophilic organic colloid such as gelatin Belgian Pat. No. 722,298, French Pat. No. 1,599,790, and the like and has a low molecular weight, is capable Japanese Pat. Publica 291 30/1964 d of easily dissolving the silver halide developing agent, is 38 Representative mples of xili ry substantially water-insoluble and preferably has a boildeveloping agents are phenylhydroquinone,2-hydroxyi poinlt hi h than b t 150C, Th hi h b iling phetilzyIhyldrocl liliircilonq phenoiiylltiycggotc lumone, hth4- solvent is normally a liquid or a low melting solid at me yp eny y roquinone, 1 y roxynap aroom temperature. 16116, p y y q As the high boiling solvent, the following can be 2-(4-aminophenethyl)-5-methylhydroquinone, 4- aminophenethylhydroquinone, 2,5-dimethoxyhydroquinone, 2,S-dibutoxyhydroquinone, m-xylohydroquinone, brornohydroquinone, 3,6-dichlorohyused: phosphoric acid esters such as triethyl phosphate, tri-n-butyl phosphate, triphenyl phosphate, tricresyl phosphate, tri-p-tert-butylphenyl phosphate, tri-2- ethylhexyl phosphate, and the like; phthalic acid esters such as methyl phthalate, ethyl phthalate, n-butyl phthalate, 2-ethylbutyl phthalate, n-propyl phthalate, n-amyl phthalate, isoamyl phthalate, n'-octyl phthalate, B-methoxyethyl phthalate, ditetrahydrofurfuryl phthalate and the like; aliphatic dibasic acid esters such as ditetrahydrofurfuryladipate, n-octyladipate, 2-ethylhexyladipate, n-hexyladipate, 2-ethylbutylacelate, butylsebacate, ditetrahydrofurfurylsuccinate, dibutox yethylsuccinate, and the like; aliphatic monobasic acid esters such as oleic acid butyl ester, oleic acid tetrahydrofurfuryl ester, o-methoxyphenyl acetate, stearic acid butyl ester and the like; other esters such as triethyl citrate, acetyltriethyl citrate, triethyleneglycol di-2-ethyl hexoate, acetylricinol acid methyl ester, acetylricinol acid methoxyethyl ester, 'y-acetoxybutylacetyl succinate, tetrahydrofurfuryl benzoate, and the like; amides and imides such as diethyl lauryl amide, dibutyl lauryl amide, tetraethyl phthalarnide, N-n-butyl acetanilide, N-methyl-p-methyl acetanilide, N-n-amyl succinimide, N-n-amyl phthalimide, lauloyl piperidine, and the like; alcohols such as 4-methyl-2-pentanol, furfuryl alcohol, methyl isobutyl carbinol, 2,4-di-namyl phenol, and the like; ethers such as ethyleneglycol monobenzyl ether; and ketones such as ethyl-N, N-din-butylcarbamate, 2-methyl cyclohexanone, 3-methyl cyclohexanone, 4-methyl cyclohexanone, and the like,

etc.

The auxiliary solvent is effective in that when used in combination with the high boiling solvent, the solubility of the dye developer and the auxiliary developing agent is increased and the grain size of the dispersion is reduced. The auxiliary solvent can be removed from the dispersion containing the high boiling solvent by airdrying or washing. 1

Representative examples of auxiliary solvents are esters such as fl-ethoxyethyl acetate, fi-butoxy-B-ethoxyethyl acetate, tetrahydrofurfuryl adipate, ethyleneglycol monoacetate, methoxy triglycol acetate, ethyleneglycol monomethyl ether acetate, methyl acetate, ethyl acetate, propyl acetate, butyl acetate, isopropyl acetate, ethyl propyonate, and the like; alcohols such as diacetone alcohol, ethylene ,glycol, diethylene glycol,

- dipropylene alcohol, sec-butyl, alcohol, benzyl alcohol and the like; ketones such as methyl isobutyl ketone, methyl isopropyl ketone, acetonylacetone, cyclohexanone, 2-methylcyclohexanone, ;3-rnethylcyclohexanone, 4-methylcyclohexanone, and the like; ethers such as diethylene glycol monobutyl ether, ethylene glycol monobutyl ether, diethylene glycol monoethyl ether, ethylene glycol monomethyl ether and the like; carbon tetrachloride and chloroform; etc.

The ratio of the silver halide developing agent to the binder ispreferably in the range of about 2:1 to 1:2.

The dispersion of the present invention can contain, if desired, other additives.

For example, by adding an oleophilic polymer to the oil phase of the dispersion, the stability of the dispersion can be increased. Suitable examples thereof include polyvinyl acetate, polyvinyl butyral, polyvinyl chloride, polyvinyl propionate, polymethyl acrylate, polyethyl acrylate, polybutyl acrylate, polypropyl acrylate, polymethylmethacrylate, polyethylmethacrylate, polybutylmethacrylate, polypropylmethacrylate, etc. In addition by adding a viscosity increasing agent, the stability of the dispersion can be increased. Representative examples there of include polyacrylamide, cellulose nitrate, poly-p-sulfostyrene potassium salt, etc. Further, after the dispersion is coated, a hardening agent such as' formaldehyde, mucochloric acid, 2- hydroxyl-4,6-dichloro-s-triazine sodium salt, etc., can be added to harden the coated layer.

The silver halide developing agent of the present invention is rendered free from the separation of the silver halide developing agent and coarse-graining of the fine liquid particles of the water-insoluble solvent in which the silver halide developing agent is contained, for a long period of time, and thus it is quite stable.

The dispersion of the present invention can be employed in the photographic elements disclosed in U.S.

Pat. Nos. 2,983,606, 3,415,644, 3,415,645, 3,415,646,

3,594,164, and 3,594,165 and in the photographic materials as disclosed in U.S. Pat. Nos. 2,983,606, 3,345,163, 3,188,209 and 3,316,090. a

The present invention will be described in greater detail by reference to the following examples. Unless otherwise indicated, all parts, percents, ratios, and the like are by weight.

EXAMPLE 1 To a mixture of 15 ml of N,N-diethyl lauryl amide and 22 ml of cyclohexanone was added 10 g of yellow dye developer: 1-phenyl-3-N-n-hexylcarbamoyl-4-p- (2-hydroquinonylethyl)phenylazo-S-pyrazolone. To the resulting solution, a 20% cyclohexanone solution of Compound 2 having an average molecular weight of about 4000 (in the amounts shown in Table 1) as the emulsifying agent and 2 ml of a 20% methanol solution of Span 20 (sorbitan monolauric acid ester produced by Atlas Powder Co.) were added and completely dissolved in the vicinity of about C.

The solution so prepared was added to g of a 10% aqueous solution of gelatin at about 80C and stirred moderately. The resulting solution was dispersed with a colloid mill. The dispersion so prepared was cool-set and stored. The average grain size was about 0.3 to 0.4 u.

The emulsion was coated on a gelatin undercoated cellulose triacetate base in a thickness of about 3 p, and on the resulting layer a gelatin aqueous solution having the following composition was coated to provide a dry thickness of about 1 ,u,.

10% Gelatin Aqueous Solution 40 g Water ml 5% Polyoxyethylenesorbitan Monolauryl 8 ml Ester Aqueous Solution 1% Mucochloric Acid Aqueous Solution 1 ml The sample so prepared was stored under the conditions of 50C and 80% RH and the days until crystals of the dye developer separated were measured.

The results obtained are shown in Table 1.

Table 1 Amount of Compound 2 Days until Crystals of the Yellow Dye Developer Separated EX M EXAMPLE6 The procedureiof Example 1 was repeated using 10 g of magenta dye developer: 2-p-(2 magenta dye developerz'. 2-p-(2-hydroquinonylethyl)- hydroquinonylethyl)-phenylazo-4-isopropoxy-l -naphphenylazo-4-isopropoxy-l-naphthol. I thol was added to 60 ml of 2-methylcyclohexanone. To

I The results obtained are, shown in Table 2. the resulting solution, 5 g of polyvinyl hydrogen phthalate, 5 g of Compound 2 as the emulsifying agent, and 2 T bl 2 I g 6 ml of a 20% methanol solution of Span 20 were added Amount of Compound 2 DaysDuntilJCryIstaIS of the Magenta d di l d i h i i i f 80C.

I ye Separated The resulting solution was added to 160 g of a 10% GET gi -5 gelatin aqueous solution at about 80C and stirred 3 moderately. The solution was further dispersed using a 1.2 More than 10 colloid min,v 1

' The dispersion was cool-set and stored. The resulting emulsion was coated on a gelatin subbed cellulosetri- EXAMPLE 3 acetate base in a thickness of about 3 p. and gelatin was I h p pq m o Example 1 was cp using ya cozted on the layer as prepared above m a thickness vof I ggig ii t '(hydroqumonylpropyl)ammq The resulting sample was stored under the conditions 1 Y fi i T 51 I l of 50C and 80% RH and the days until Crystal of the e ts o l f Y m a e dye developer separated, were measured. The crystals Table 3 of the dye developer did not separate for more than 10 Amount of Compound 2 Days until Crystals of 'the Cyan Dye days" 1, Developer Separated EXAMPLE 1 gg (dalys) I The procedure of Example 2 was repeated except 0.8 2 that Aerogel OT (bis-(2-ethylhexyl)sulfosuccinic acid- 2 3 sodium salt produced by American Cyanamid Co.) was used as the emulsifying agent and as magenta dye developer; 2-p-(2-hydroquinonylethyl)-phenylazo-4-iso- EXAMPLE 4 i propoxy-l-naphthol, was used. The results obtained are shown in Table 6. The procedure'of Example 1 was repeated using T bl 6 magenta' dye developer: l-acetoxy-2-p-( 2- y qu y y )-p y p p yph-' Amount of Aerosol or Days until Crystals of the Ma enta 1 Dye Developer Separate thale ne.

The results are shown in Table 4. r s (days) I V I Z 1. o 4 Within 1 Table 4 0.8 Within 1 Amount of Compound 2 Days unt l Crystals of the'Magenta Dye Developer Separated 40 (grams) I V COMPARISON EXAMPLE 2 8:; i Moreth'afi V The procedure of Example 2 was repeated except 1.2 More than 10 that p-nonylphenoxypropylsulfonic acid sodium salt was used as the'emulsifying agent and dispersed in a l0% gelatin aqueous solution and that magenta dye developer; 2-p-(2-hydroquinonylethyl)-phenylazo-4- EXAMPLE 5 isopropoxy l-naphthol, was used. The procedure of Example 2 was repeated except The results obtained are shown in Table 7.

. Table 7 Amount of p-Nonylphenoxypropyl Days until Crystals of the Sulfonic Acid Sodium Salt Magenta Dye Developer Separated (grams) (days) 0.4 Within 1 0.8 Within 1 1.2 I Within 1 that Compound 14 having an average molecular-weight COMPARISON EXAMPLE 3 f 3000:1218 T i ii The procedure of Example 4 was repeated using z eve Opel" 1 roqumogy Aerosol OT as the emulsifying agent and magenta dye t y )1) my am? "sopropoxy' t 0 was use developer; l-acetoxy-2-[p-( 2-hydroquinolyethyl)- The results obtained are shown in Table 5. p y 1- p p yp A v The results obtained are shown in Table 8.

Table 5' i Table 8 Amount of Compound 14 I Days until Crystals of the Magenta Amount of Aerosol OT Days until Crystals of the Magenta Dye Developer Separated Dye Developer Separated (grams) (days) I (grams) (days) 0.4 l 0.4 Within l 0.8 2 0.8 Within 1 1.2 5 [.2 Within 1 By comparing Examples 1 m6 with Comparison Examples 1 to 3, it can be seen that the polymers of the present invention are quite effective in preventing the separation of crystals of the dye developer.

While the invention has been described in detail an with reference to specific embodiments thereof, it will be apparent to one skilled in the art that various changes and modifications can be made therein without departing from the spirit and scopethereof. 1

What is claimed is: r

l. A silver halide developing agent dispersion which comprises a hydrophilic organic colloid having 'dispersed therein fine droplets of a silver halide developing agent dissolved in av substantially water-insoluble solvent, and at least one surface active polymer selected from the group consisting of the compounds represented by the following formulae (ll) and (Ill):

and

wherein R is a hydrocarbon chain or a fluorine substituted hydrocarbon chain containing 4 to 22 carbon atoms or an aryl group, n is O or an integer of l to 40, and M is a hydrogen atom or a cation; and wherein the molar ratio of x to y ranges from 3:1 to 9:1. V

2. The silver halide developing agent dispersion according to claim 1, wherein the surface active polymer has the general formula wherein R, n, M, x and y are as defined in claim 2.

3. The silver halide developing agent dispersion according to claim 1, wherein the amount of the surface active polymer ranges from about 0.5 to 50% by weight based on the silver halide developing agent.

4. The silver halide developing agent dispersion according to claim 1, wherein the silver halide developing agent comprises at least one dye developer.

5. The silver halide developing agent dispersion according to claim 1, wherein the silver halide developing agent comprises at least-one dye developer and at least one auxiliary developing agent.

6. The silver halide developing agent dispersion according to claim 1, wherein a solution of the silver halide developing agent in a high boiling solvent is dispersed in about 1 to by weight aqueous solution of the hydrophilic organic colloid.

7. The silver halide developing agent dispersion according to claim 1, wherein the hydrophilic organic colloid is gelatin.

8. The silver halide developing agent dispersion according to claim 1, wherein the surface active polymer is selected from the group consisting of compounds represented by the following formulae:

CH 0 Hook COO(CH CH O)C-,Fi5(n) wherein the molar ratio of x to y ranges from 3:1 to 9: l.

9. Thesilver halide developing agent dispersion according to claim 1, wherein the surface active polymer has i a molecular weight from about 250 to about "10. The silver halide developing agent dispersion according to claim 1, wherein the surface active polymer has a molecular weight from about 1,000 to 20,000.

11. The silver halide developing agent dispersion according to claim 2, wherein the surface active polymer is selected from the group consisting of compounds represented by the following formulae:

1! Na JIOOC HMn) and wherein the molar ratio ofx to y ranges from 3:1 to 9:1.

12. The silver halide developing agent dispersion according to claim 2, wherein the surface active polymer has a molecular weight from about 250 to 100,000.

13. The silver halide developing agent dispersion according to claim 2, wherein thesurface active polymer has a molecular weight from about 1,000 to 20,000.

14. The silver halide developing agent dispersion according to claim 1, wherein the dispersion further contains an anionic or nonionic surface active agent.

15. The silver halide developing agent dispersion according to claim 14, wherein the surface active agent is selected fromthe group consisting of aliphatic acid salts, alkylsulfates, alkylphosphates, alkyl-sulfonates, alkylarylsulfonates, formaldehyde-condensates with alkyl-naphthalenesulfonates, alkyldiphenyl-ether sulfonates, dialkylsulfosuccinates, polyoxyethylene, alkyl ethers and the sulfuric ester salts thereof, poly-oxyethylene alkylaryl ethers and the sulfuric ester salts thereof, poly-oxyethylene alkyl esters and the surfuric ester salts thereof, sorbitan alkyl esters, polyoxyethylene sorbitan alkyl esters, polyoxyethylene mannitan monolauric acid ester and styrcne-maleic acid half 65 ester copolymer. I

16. The silver halide developing agent dispersion according to claim 14 wherein the surface active agent is selected from the group consisting of sodium m'yris-.

tate, sodium palmitate, sodium steara-te, sodium oleate, sodium linoleate, sodium laurate, sodium caprate, p0- tassium laurate, potassium steara'te, sodium octadecylsulfate, sodium decylsulfate, sodium dodecylsulfate, sodium tetradecylsulfate, sodium hexadecylsulfate, potassium decylsulfate, potassium oleylsulfate, sodium octylphosphate, sodium dioctylphosphate, sodium nonylphosphate, sodium decylphosphate, potassium undecylphosphate, potassium dodecylphosphate, potassium pentadecylphosphate, sodium dodecylsulfonate, sodium hexadecanesulfonate, sodium octadecanesulfonate, potassium octylbenzenesulfonate, sodium nonylbenzenesulfonate, sodium decylbenzenesulfonate, sodium undecylsulfonate, sodium dodecylbenzenesulfonate, sodium tridecylbenzenesulfonate, sodium dibutylnaphthalenesulfonate, sodium decylnaphthalenesulfonate, sodium octylnaphthalenesulfonate, potassium pentylnaphthalenesulfonate, sodium formaldehyde-condensate with naphthalenesulfonate, sodium formaldehyde-condensate with butyl-naphthalensulfonate, sodium nonyldiphenylether sulfonate, sodium decyldiphenylether sulfonate, sodium dodecyldiphenylether disulfonate, sodium dihexylsulfosuccinate, sodium dioctylsulfosuccinate, sodium dinonylsulfosuccinate, polyoxyethylene lauryl ether, polyoxyethylene oleyl ether, sodium polyoxyethylene lauryl ether sul-' fate, sodium polyoxyethylene oleyl ether sulfate, polyoxyethylene dodecyl ether, polyoxyethylene tetradecyl ether, polyoxyethylene hexadecyl ether, polyoxyethylene octadecyl ether, sodium polyoxyethylene nonylphenyl ether sulfate, polyoxyethylene nonylphenyl ether, sodium polyoxyethylene dibutylphenyl ether sulfate, polyoxyethylene stearic acid ester, polyoxyethylene palmitic acid ester, sodium polyoxyethylene stearic acid ester sulfate, sodium polyoxyethylene lauric acid ester sulfate, sodium polyoxyethylene capric acid ester sulfate, sodium polyoxyethylene myristic acid ester sulfate, sorbitan monostearic acid ester, sorbitan tristearic acid ester, sorbitan monooleic acid ester, sodium sorbitan trioleate, polyoxyethylene sorbitan monolauric acid ester, polyoxyethylene sorbitan monostearic acid ester, polyoxyethylene monooleic acid ester, polyoxyethylene sorbitan monopalmitic acid ester, poly-oxyethylene trioleic acid ester, polyoxyethylene mannitan monolauric acid ester and styrenemaleic acid half ester copolymer.

17. The silver halide developing agent dispersion according to claim 4, wherein the dye developer is selected from the group consisting of l-Phenyl-3-N-nhexylcarbamoyl-4-p-(2-hydroquinonylethyl)- phenylazo-S-pyrazolone, 2-p-(2-Hydroquinonylethyl)- phenylazo-4-isopropoxyl -naphthol, l ,4-bis[B-)Hydroquinonyl-isopropyl)amino]-5,8 -dihydroxyanthraquinone, 1-Phenyl-3-n-butyl-carbamoyl-4-[ p- (2 5 -dihydroxyphenethyl )-phenylzao ]-5 -pyrazolone, lPhenyl-3-N-n-hexyl-carbamoyl 4-[p-( 2', 5 ,'-dihydroxyphenethyl)-phenylazol]-5-pyrazolone, 2, [p-(2, 5 '-Dihydroxyphenethyl)phenylazo]-4-isopropoxy-1- naphthol, l-Phenyl-3-N-cycl0hexylcarbarnoyl-4-[p- (2 5 '-dihydroxy-phenethyl )-phenylazo]-5-pyrazolone, l-Phenyl-3-amido-4 4'[p-2", 5"-dihydroxyphenethyl)-phenylzao -2,5'-diethoxyphenylazo -5- pyrazolone, l-Phenyl-3-N-cyclohexylcarbamoyl-4-[p- 5 -dihydroxy-phenethyl )-phenylazc]-5-pyrazolone, l-Phenyl-3 phenyl-4-[p-(2", 5'-'dihydroxyphenethyl)-phenylazo]-5-pyrazolone, l Phenyl-3-methyl-4- [p-l, 5-dihydroxyphenethyl)-phenylazoI-S-pyrazolone, l-Phenyl-3-(N n-heptyl)carbarnoyl-4-[p-(B- hydroquinone, 4-aminophenethylhydroquinone, 2,5- dimethoxyhydroquinone, 2,5-dibutoxyhydroquinone, m-xylohydroquinone, bromohydroquinone, 3,6- dichlorohydroquinone, 2-dimethylaminomethyltoluhydroquinone, 2-cyclohexylhydroquinone, sec-butylhydroquinone, 2,S-dichlorohydroquinone, 2,5,-diisopropylhydroquinone, 2,5-diiodohydroquinone, 3- chlorotoluhydroquinone, tetrachlorohydroquinone, 2,5-diphenylhydroquinone, 2,5-diresorcylhydroquinone, 2,5-dioctylhydroquinone, dodecylhydroquinone, 4-methoxycatechol, 4-isopropoxycatechol, 3-isopropylcatechol, 4-phenylcatechol, 3,6-dimethylcatechol and l,2 dihydroxy-5,8-methano-5,6,7,9-tetrahydronaphthalene.

19. The silver halide developing agent dispersion according to claim 6, wherein the high boiling solvent has a boiling point above 150 C.

20. The silver halide developing agent dispersion according to claim 19, wherein the solution of the silver halide developing agent in a high boiling solvent is dispersed in the form of fine colloidal particles.

21. The, silver halide developing agent dispersion according to claim 20, wherein the colloidal particles have a particle size of less than about 1p 22. The silver halide developing agent dispersion according to claim 20, wherein the colloidal particles have a particle size of less than about 0.3;).-

23. The silver halide developing agent dispersion according to claim 1, wherein the hydrophilic organic colloid is selected from the group consisting of phthalated gelatin, polyvinyl alcohol, polyvinyl pyrrolidone, polyacrylamide, sodium polyacrylate, polyvinyl- 2-methyldiazole, acrylamide/l -vinyl-2- methylimidazole copolymers, acrylamide/imidazole copolymers, acrylamide/l -vinyl-2-methylimidazole/acrylic acid copolymers, nitrocarboxymethylcellulose, N-vinylpyrrolidone-acrylic acid copolymers, N-vinylpyrrolidone-acrylic acid-methylacrylate copolymers, vinylphthalimide-acrylic acid copolymers, cellulose acetate hydrogen phthalate, poly-N-methylmethacrylamide, dimethyl-aminoethylmethacrylateacrylic acid copolymers, dimethylamino-ethylmethacrylate-acrylic acid-butyl acrylate copolymers, N,N-diethylacrylamide-acrylamide copolymers, poly-N-methylacrylamide copolymers, N-methylacrylamide-N-hydroxymethylacrylamide copolymers, poly-N-ethylacrylamide, 'rnethylvinylketoneac'rylamide copolyers and N-vinylpyrrolidone-methacrolein copolymers.

24. The silver halide developing agent dispersion according to claim 19, wherein the high boiling solvent is selected from the group consisting of phosphoric acid esters, phthalic acid esters, aliphatic dibasic acid esters, aliphatic monobasic acid esters, amides, imides, alcohols, ethers, ketones.

25. The silver halide developing agent dispersion according to claim 19, wherein the high boiling solvent is selected from the group consisting of triethyl phosphate, tri-n-butyl phosphate, triphenyl phosphate, tricresyl phosphate, tri-p-tertbutylphenyl phosphate, tri- 2-ethylhexyl phosphate, methyl phthalate, ethyl phthalate, n-butyl phthalate, 2 ethylbutyl phthalate, n-propyl phthalate, n-amyl phthalate, isoamyl phthalate, n-octyl phthalate, fl-methoxyethyl phthalate, ditetrahydrofurfuryl phthalate, ditetrahydrofurfuryladipate, noctyladipate, Z-ethylhexyladipate, n-hexyladipate, 2- ethylbutyl-acelate, butylsebacate, ditetrahydrofurfurylsuccinate, dibutoxyethylsuccinate, oleic acid butyl cster, oleic acid tetrahydrofurfuryl ester, o-methoxyphenyl acetate, stearic acid butyl ester, triethyl citrate, acetyltriethyl citrate, triethyleneglycol di-Z-ethyl hexoate, acetylricinol acid methyl ester, acetylricinol acid methoxyethyl ester, a-acetoxy-butylac'etyl succinate, tetrahydrofurfuryl benzoate, diethyl lauryl aminde, dibutyl lauryl amide, tetraethyl phthalamide, N-n-butyl acetanilide, N-methyl-p-methyl acetanilide, 'N-n-amyl succinimide,'N-n-amyl phthalimide, lauloyl piperidine, 4-methyl-2-pentanol, furfuryl alcohol, methyl isobutyl carbinol, 2,4-di-n-amyl phenol, and the like; ethers such as ethyleneglycol monobenzyl ether; and ketones such as ethyl-N, N-di-n-butylcarbamate, Z-methyl cyclohexanone, 3-methyl cyclohexanone and 4-methyl cyclohexanone.

26. The silver halide developing agent dispersion according to claim 1, wherein the ratio of the silver halide developing agent to the hydrophilic organic colloid is in the range of about 2:1 to 1:2.

27. The silver halide developing agent dispersion according to claim 19, wherein the high boiling solvent is capable of easily dissolving the silver halide developing agent and is substantially water-insoluble.

28. The silver halide developing agent dispersion according to claim 27, wherein the solution of the silver halide developing agent further contains an oleophilic polymer.

29. The silver halide developing agent dispersion according to claim 28, wherein the oleophilic polymer is selected from the group consisting of polyvinyl acetate, polyvinyl butyral, polyvinyl chloride, polyvinyl propionate, polymethyl acrylate, polyethyl acrylate, polybutyl acrylate, polypropyl acrylate, polymethylmethacrylate, polyethylmethacrylat'e, polybutylmethacrylate and polypropylmethacrylate.

30. The silver halide developing agent dispersion according to claim 28, wherein the dispersion further contains a viscosity increasing agent.

31. The silver halide developing agent dispersion according to claim 30, wherein the viscosity increasing agent is selected from the group consisting of polyacrylamide, cellulose nitrate, and poly-p-sulfostyrene potassium salt.

32. The silver halide developing agent dispersion according to claim 2, wherein the amount of the surface active polymer ranges from about 0.5 to 50% by weight based on the silver halide developing agent.

33. The silver halide developing agent dispersion according to claim 2, wherein the silver halide developing agent comprises at least one dye developer.

34. The silver halide developing agent dispersion according to claim 2, wherein the silver halide developing agent comprises at least one dye developer and at least one auxiliary developing agent.

35. The silver halide developing agent dispersion according to claim 2, wherein a solution of the silver halide developing agent in a high boiling solvent is dispersed in an about 1 to 20% by weight aqueous solution of the hydrophilic organic colloid.

36. The silver halide developing agent dispersion according to claim 2, wherein the hydrophilic organic colloid is gelatin.

37. The silver halide developing agent dispersion according to claim 2, wherein'th'e dispersion further contains an anionic or no'nionic surface active agent.

38. The-silver halide developing agentdispersion' according to claim 37,wherein the surface active agent is selected from the group consisting of aliphatic acid 

1. A SILVER HALIDE DEVELOPING AGENT DISPERSION WHIH COMPRISES A HYDROPHILIC ORGANIC COLLOID HAVING DISPERSED THEREIN FINE DROPLETS OF A SILVER HALIDE DEVELOPING AGENT DISSOLVED IN A SUBSTANTIALLY WATER-INSOLUBLE SOLVENT, AND AT LEAST ONE SURFACE ACTIVE POLYMER SELECTED FROM THE GROUP CONSISTING OF THE COMPOUNDS REPRESENTED BY THE FOLLOWING FORMULAE (II) AND (III):
 2. The silver halide developing agent dispersion according to claim 1, wherein the surface active polymer has the general formula
 3. The silver halide developing agent dispersion according to claim 1, wherein the amount of the surface active polymer ranges from about 0.5 to 50% by weight based on the silver halide developing agent.
 4. The silver halide developing agent dispersion according to claim 1, wherein the silver halide developing agent comprises at least one dye developer.
 5. The silver halide developing agent dispersion according to claim 1, wherein the silver halide developing agent comprises at least-one dye developer and at least one auxiliary developing agent.
 6. The silver halide developing agent dispersion according to claim 1, wherein a solution of the silver halide developing agent in a high boiling solvent is dispersed in about 1 to 20% by weight aqueous solution of the hydrophilic organic colloid.
 7. The silver halide developing agent dispersion according to claim 1, wherein the hydrophilic organic colloid is gelatin.
 8. The silver halide developing agent dispersion according to claim 1, wherein the surface active polymer is selected from the group consisting of compounds represented by the following formulae:
 9. The silver halide developing agent dispersion according to claim 1, wherein the surface active polymer has a molecular weight from about 250 to about 100,000.
 10. The silver halide developing agent dispersion according to claim 1, wherein the surface active polymer has a molecular weight from about 1,000 to 20,000.
 11. The silver halide developing agent dispersion according to claim 2, wherein the surface active polymer is selected from the group consisting of compounds represented by the following formulae:
 12. The silver halide developing agent dispersion according to claim 2, wherein the surface active polymer has a molecular weight from about 250 to 100,000.
 13. The silver halide developing agent dispersion according to claim 2, wherein the surface active polymer has a molecular weight from about 1,000 to 20,000.
 14. The silver halide developing agent dispersion according to claim 1, wherein the dispersion further contains an anionic or nonionic surface active agent.
 15. The silver halide developing agent dispersion according to claim 14, wherein the surface active agent is selected from the group consisting of aliphatic acid salts, alkylsulfates, alkylphosphates, alkyl-sulfonates, alkylarylsulfonates, formaldehyde-condensates with alkyl-naphthalenesulfonates, alkyldiphenyl-ether sulfonates, dialkylsulfosuccinates, polyoxyethylene, alkyl ethers and the sulfuric ester salts thereof, poly-oxyethylene alkylaryl ethers and the sulfuric ester salts thereof, poly-oxyethylene alkyl esters and the surfuric ester salts thereof, sorbitan alkyl esters, polyoxyethylene sorbitan alkyl esters, polyoxyethylene mannitan monolauric acid ester and styrene-maleic acid half ester copolymer.
 16. The silver halide developing agent dispersion according to claim 14 wherein the surface active agent is selected from the group consisting of sodium myristate, sodium palmitate, sodium stearate, sodium oleate, sodium linoleate, sodium laurate, sodium caprate, potassium laurate, potassium stearate, sodium octadecylsulfate, sodium decylsulfate, sodium dodecylsulfate, sodium tetradecylsulfate, sodium hexadecylsulfate, potassium decylsulfate, potassium oleylsulfate, sodium octylphosphate, sodium dioctylphosphate, sodium nonylphosphate, sodium decylphosphate, potassium undecylphosphate, potassium dodecylphosphate, potassium pentadecylphosphate, sodium dodecylsulfonate, sodium hexadecanesulfonate, sodium octadecanesulfonate, potassium octylbenzenesulfonate, sodium nonylbenzenesulfonate, sodium decylbenzenesulfonate, sodium undecylsulfonate, sodium dodecylbenzenesulfonate, sodium tridecylbenzenesulfonate, sodium dibutylnaphthalenesulfonate, sodium decylnaphthalenesulfonate, sodium octylnaphthalenesulfonate, potassium pentylnaphthalenesulfonate, sodium formaldehyde-condensate with naphthalenesulfonate, sodium formaldehyde-condensate with butyl-naphthalensulfonate, sodium nonyldiphenylether sulfonate, sodium decyldiphenylether sulfonate, sodium dodecyldiphenylether disulfonate, sodium dihexylsulfosuccinate, sodium dioctylsulfosuccinate, sodium dinonylsulfosuccinate, polyoxyethylene lauryl ether, polyoxyethylene oleyl ether, sodium polyoxyethylene lauryl ether sulfate, sodium polyoxyethylene oleyl ether sulfate, polyoxyethylene dodecyl ether, polyoxyethylene tetradecyl ether, polyoxyethylene hexadecyl ether, polyoxyethylene octadecyl ether, sodium polyoxyethylene nonylphenyl ether sulfate, polyoxyethylene nonylphenyl ether, sodium polyoxyethylene dibutylphenyl ether sulfate, polyoxyethylene stearic acid ester, polyoxyethylene palmitic acid ester, sodium polyoxyethylene stearic acid ester sulfate, sodium polyoxyethylene lauric acid ester sulfate, sodium polyoxyethylene capric acid ester sulfate, sodium polyoxyethylene myristic acid ester sulfate, sorbitan monostearic acid ester, sorbitan tristearic acid ester, sorbitan monooleic acid ester, sodium sorbitan trioleate, polyoxyethylene sorbitan monolauric acid ester, polyoxyethylene sorbitan monostearic acid ester, polyoxyethylene monooleic acid ester, polyoxyethylene sorbitan monopalmitic acid ester, poly-oxyethylene trioleic acid ester, polyoxyethylene mannitan monolauric acid ester and styrenemaleic acid half ester copolymer.
 17. The silver halide developinG agent dispersion according to claim 4, wherein the dye developer is selected from the group consisting of 1-Phenyl-3-N-n-hexylcarbamoyl-4-p-(2-hydroquinonylethyl)-phenylazo-5 -pyrazolone, 2-p-(2-Hydroquinonylethyl)-phenylazo-4-isopropoxy-1-naphthol, 1,4-bis( Beta -)Hydroquinonyl-isopropyl)amino)-5,8-dihydroxy-anthraquinone, 1-Phenyl-3-n-butyl-carbamoyl-4-(p-(2'', 5''-dihydroxyphenethyl)-phenylzao)-5-pyrazolone, 1-Phenyl-3-N-n-hexyl-carbamoyl-4-(p-(2'', 5,''-dihydroxyphenethyl)-phenylazol)-5-pyrazolone, 2, (p-(2'', 5''-Dihydroxyphenethyl)phenylazo)-4-isopropoxy-1-naphthol, 1-Phenyl-3-N-cyclohexylcarbamoyl-4-(p-(2'', 5''-dihydroxy-phenethyl)-phenylazo)-5-pyrazolone, 1-Phenyl-3-amido-4 (4''(p-2'''', 5''''-dihydroxyphenethyl)-phenylzao)-2'',5''-diethoxyphenylazo)-5-pyrazolone, 1-Phenyl-3-N-cyclohexylcarbamoyl-4-(p-(2'', 5''-dihydroxy-phenethyl)-phenylazc)-5-pyrazolone, 1-Phenyl-3-phenyl-4-(p-(2'', 5''-dihydroxyphenethyl)-phenylazo)-5-pyrazolone, 1-Phenyl-3-methyl-4-(p-1'', 5''-dihydroxyphenethyl)-phenylazo)-5-pyrazolone, 1-Phenyl-3-(N-n-heptyl)carbamoyl-4-(p-( Beta -hydroquinonylethyl)-phenylazo)-5-pyrazolone, 1-(2''-Chlorophenyl)-3-(N-n-hexylcarbamoyl)-4-(p-( Beta -hydroquinonylethyl)-phenylazo(-5-pyrazolone,
 18. The silver halide developing agent dispersion according to claim 5, wherein the auxiliary developing agent is selected from the group consisting of phenylhydroquinone, 2-hydroxyphenylhydroquinone, phenoxyhydroquinone, 4-methylphenyl-hydroquinone, 1,4-dihydroxynaphthalene, 2-(4-aminophenethyl)-5-bromohydroquinone, 2-(4-aminophenethyl)-5-methylhydroquinone, 4-aminophenethylhydroquinone, 2,5-dimethoxyhydroquinone, 2,5-dibutoxyhydroquinone, m-xylohydroquinone, bromohydroquinone, 3,6-dichlorohydroquinone, 2-dimethylaminomethyltoluhydroquinone, 2-cyclohexylhydroquinone, sec-butylhydroquinone, 2,5-dichlorohydroquinone, 2,5,-diisopropylhydroquinone, 2,5-diiodohydroquinone, 3-chlorotoluhydroquinone, tetrachlorohydroquinone, 2,5-diphenylhyDroquinone, 2,5-diresorcylhydroquinone, 2,5-dioctylhydroquinone, dodecylhydroquinone, 4-methoxycatechol, 4-isopropoxycatechol, 3-isopropylcatechol, 4-phenylcatechol, 3,6-dimethylcatechol and 1, 2-dihydroxy-5,8-methano-5,6,7,9-tetrahydronaphthalene.
 19. The silver halide developing agent dispersion according to claim 6, wherein the high boiling solvent has a boiling point above 150* C.
 20. The silver halide developing agent dispersion according to claim 19, wherein the solution of the silver halide developing agent in a high boiling solvent is dispersed in the form of fine colloidal particles.
 21. The silver halide developing agent dispersion according to claim 20, wherein the colloidal particles have a particle size of less than about 1 Mu .
 22. The silver halide developing agent dispersion according to claim 20, wherein the colloidal particles have a particle size of less than about 0.3 Mu .
 23. The silver halide developing agent dispersion according to claim 1, wherein the hydrophilic organic colloid is selected from the group consisting of phthalated gelatin, polyvinyl alcohol, polyvinyl pyrrolidone, polyacrylamide, sodium polyacrylate, polyvinyl-2-methyldiazole, acrylamide/1-vinyl-2-methylimidazole copolymers, acrylamide/imidazole copolymers, acrylamide/1-vinyl-2-methylimidazole/acrylic acid copolymers, nitrocarboxymethylcellulose, N-vinylpyrrolidone-acrylic acid copolymers, N-vinylpyrrolidone-acrylic acid-methylacrylate copolymers, vinylphthalimide-acrylic acid copolymers, cellulose acetate hydrogen phthalate, poly-N-methylmethacrylamide, dimethyl-aminoethylmethacrylateacrylic acid copolymers, dimethylamino-ethylmethacrylate-acrylic acid-butyl acrylate copolymers, N,N-diethylacrylamide-acrylamide copolymers, poly-N-methylacrylamide copolymers, N-methylacrylamide-N-hydroxymethylacrylamide copolymers, poly-N-ethylacrylamide, methylvinylketoneacrylamide copolyers and N-vinylpyrrolidone-methacrolein copolymers.
 24. The silver halide developing agent dispersion according to claim 19, wherein the high boiling solvent is selected from the group consisting of phosphoric acid esters, phthalic acid esters, aliphatic dibasic acid esters, aliphatic monobasic acid esters, amides, imides, alcohols, ethers, ketones.
 25. The silver halide developing agent dispersion according to claim 19, wherein the high boiling solvent is selected from the group consisting of triethyl phosphate, tri-n-butyl phosphate, triphenyl phosphate, tricresyl phosphate, tri-p-tertbutylphenyl phosphate, tri-2-ethylhexyl phosphate, methyl phthalate, ethyl phthalate, n-butyl phthalate, 2-ethylbutyl phthalate, n-propyl phthalate, n-amyl phthalate, isoamyl phthalate, n-octyl phthalate, Beta -methoxyethyl phthalate, ditetrahydrofurfuryl phthalate, ditetrahydrofurfuryladipate, n-octyladipate, 2-ethylhexyladipate, n-hexyladipate, 2-ethylbutyl-acelate, butylsebacate, ditetrahydrofurfurylsuccinate, dibutoxyethylsuccinate, oleic acid butyl ester, oleic acid tetrahydrofurfuryl ester, o-methoxyphenyl acetate, stearic acid butyl ester, triethyl citrate, acetyltriethyl citrate, triethyleneglycol di-2-ethyl hexoate, acetylricinol acid methyl ester, acetylricinol acid methoxyethyl ester, Alpha -acetoxy-butylacetyl succinate, tetrahydrofurfuryl benzoate, diethyl lauryl aminde, dibutyl lauryl amide, tetraethyl phthalamide, N-n-butyl acetanilide, N-methyl-p-methyl acetanilide, N-n-amyl succinimide, N-n-amyl phthalimide, lauloyl piperidine, 4-methyl-2-pentanol, furfuryl alcohol, methyl isobutyl carbinol, 2,4-di-n-amyl phenol, and the like; ethers such as ethyleneglycol monobenzyl ether; and ketones such as ethyl-N, N-di-n-butylcarbamate, 2-methyl cyclohexanone, 3-methyl cyclohexanone and 4-methyl cyclohexanone.
 26. The silver halide developing agent dispersion according to claim 1, wherein the ratio of the silver Halide developing agent to the hydrophilic organic colloid is in the range of about 2:1 to 1:2.
 27. The silver halide developing agent dispersion according to claim 19, wherein the high boiling solvent is capable of easily dissolving the silver halide developing agent and is substantially water-insoluble.
 28. The silver halide developing agent dispersion according to claim 27, wherein the solution of the silver halide developing agent further contains an oleophilic polymer.
 29. The silver halide developing agent dispersion according to claim 28, wherein the oleophilic polymer is selected from the group consisting of polyvinyl acetate, polyvinyl butyral, polyvinyl chloride, polyvinyl propionate, polymethyl acrylate, polyethyl acrylate, polybutyl acrylate, polypropyl acrylate, polymethylmethacrylate, polyethylmethacrylate, polybutylmethacrylate and polypropylmethacrylate.
 30. The silver halide developing agent dispersion according to claim 28, wherein the dispersion further contains a viscosity increasing agent.
 31. The silver halide developing agent dispersion according to claim 30, wherein the viscosity increasing agent is selected from the group consisting of polyacrylamide, cellulose nitrate, and poly-p-sulfostyrene potassium salt.
 32. The silver halide developing agent dispersion according to claim 2, wherein the amount of the surface active polymer ranges from about 0.5 to 50% by weight based on the silver halide developing agent.
 33. The silver halide developing agent dispersion according to claim 2, wherein the silver halide developing agent comprises at least one dye developer.
 34. The silver halide developing agent dispersion according to claim 2, wherein the silver halide developing agent comprises at least one dye developer and at least one auxiliary developing agent.
 35. The silver halide developing agent dispersion according to claim 2, wherein a solution of the silver halide developing agent in a high boiling solvent is dispersed in an about 1 to 20% by weight aqueous solution of the hydrophilic organic colloid.
 36. The silver halide developing agent dispersion according to claim 2, wherein the hydrophilic organic colloid is gelatin.
 37. The silver halide developing agent dispersion according to claim 2, wherein the dispersion further contains an anionic or nonionic surface active agent.
 38. The silver halide developing agent dispersion according to claim 37, wherein the surface active agent is selected from the group consisting of aliphatic acid salts, alkylsulfates, alkylphosphates, alkylsulfonates, alkylarylsulfonates, formaldehyde-condensates with alkylnaphthalenesulfonates, alklydiphenyl-ether sulfonates, dialkylsulfosuccinates, polyoxyethylene, alkyl ethers and the sulfuric ester salts thereof, polyoxyethylene alkylaryl ethers and the sulfuric ester salts thereof, polyoxyethylene alkyl esters and the surfuric ester salts thereof, sorbitan alkyl esters, polyoxyethylene sorbitan alkyl estere, polyoxyethylene mannitan monolauric acid ester and styrene-maleic acid half ester copolymer.
 39. The silver halide developing agent dispersion according to claim 37, wherein the surface active agent is selected from the group consisting of sodium myristate, sodium palmitate, sodium stearate, sodium oleate, sodium linoleate, sodium laurate, sodium caprate, potassium laurate, potassium stearate, sodium octadecylsulfate, sodium decylsulfate, sodium dodecylsulfate, sodium tetradecylsulfate, sodium hexadecylsulfate, potassium decylsulfate, potassium oleylsulfate, sodium octylphosphate, sodium dioctylphosphate, sodium nonylphosphate, sodium decylphosphate, potassium undecylphosphate, potassium dodecylphosphate, potassium pentadecylphosphate, sodium dodecylsulfonate, sodium hexadecanesulfonate, sodium octadecanesulfonate, potassium octylbenzenesulfonate, sodium nonylbenzenesulfonate, sodium decylbenzenesulfonate, sodium undecylsulfonate, sodium dodecylbenzenesulfonate, sodium tridecylbenzenesulfonate, sodiUm dibutylnaphthalenesulfonate, sodium decylnaphthalenesulfonate, sodium octylnaphthalenesulfonate, potassium pentylnaphthalenesulfonate, sodium formaldehyde-condensate with naphthalenesulfonate, sodium formaldehyde-condensate with butylnaphthalenesulfonate, sodium nonyldiphenylether sulfonate, sodium decyldiphenylether sulfonate, sodium dodecyldiphenylether disulfonate, sodium dihexylsulfosuccinate, sodium dioctylsulfosuccinate, sodium dinonylsulfosuccinate, polyoxyethylene lauryl ether, polyoxyethylene oleyl ether, sodium polyoxyethylene lauryl ether sulfate, sodium polyoxyethylene oleyl ether sulfate, polyoxyethylene dodecyl ether, polyoxyethylene tetradecyl ether, polyoxyethylene hexadecyl ether, polyoxyethylene octadecyl ether, sodium polyoxyethylene nonylphenyl ether sulfate, polyoxyethylene nonylphenyl ether, sodium polyoxyethylene dibutylphenyl ether sulfate, polyoxyethylene stearic acid ester, polyoxyethylene palmitic acid ester, sodium polyoxyethylene stearic acid ester sulfate, sodium polyoxyethylene lauric acid ester sulfate, sodium polyoxyethylene capric acid ester sulfate, sodium polyoxyethylene myristic acid ester sulfate, sorbitan monostearic acid ester, sorbitan tristearic acid ester, sorbitan monooleic acid ester, sodium sorbitan trioleate, polyoxyethylene sorbitan monolauric acid ester, polyoxyethylene sorbitan monostearic acid ester, polyoxyethylene monooleic acid ester, polyoxyethylene sorbitan monopalmitic acid ester, polyoxyethylene trioleic acid ester, polyoxyethylene mannitan monolauric acid ester and styrenemaleic acid half ester copolymer.
 40. The silver halide developing agent dispersion according to claim 33, wherein the dye developer is selected from the group consisting of 1-Phenyl-3-N-n-hexylcarbamoyl-4-p-(2-hydroquinonylethyl)-phenylazo-5 -pyrazolone, 2-p-(2-Hydroquinonylethyl)-phenylazo-4-isopropoxy-1-naphthol, 1,4-bis( Beta -)Hydroquinonyl-isopropyl)amino)-5,8-dihydroxy-anthraquinone, 1-Phenyl-3-n-butyl-carbamoyl-4-(p-(2'',5''-dihydroxyphenethyl)-phenylzao)-5 -pyrazolone, 1-Phenyl-3-N-n-hexylcarbamoyl-4-(p-(2'',5''-dihydroxyphenethyl)-phenylazo)-5 -pyrazolone, 2,(p-(2'',5''-Dihydroxyphenethyl)phenylazo)-4-isopropoxy-1-naphthol, 1-Phenyl-3-N-cyclohexylcarbamoyl-4-(p-(2'', 5''-dihydroxy-phenethyl)-phenylazo)-5-pyrazolone, 1-Phenyl-3-amido-4-(4''(p-2'''',5''''-dihydroxyphenethyl)-phenylzao)-2'',5'' -diethoxyphenylazo)5-pyrazolone, 1-Phenyl-3-N-cyclohexylcarbamoyl-4-(p-(2'',5''-dihydroxy-phenethyl)-phenylazo)-5-pyrazolone, 1-Phenyl-3-phenyl-4-(p-(2'',5''-dihydroxyphenethyl)-phenylazo)-5-pyrazolone, 1-Phenyl-3-methyl-4-(p-1'',5''-dihydroxyphenethyl)-phenylazo)-5-pyrazolone, 1-Phenyl-3-(N-n-heptyl)carbamoyl-4-(p-( Beta -hydroquinonylethyl)-phenylazo)-5-pyrazolone, 1-(2''-Chlorophenyl)-3-(N-n-hexylcarbamoyl)-4-(p-( Beta -hydroquinonylethyl)-phenylazo)-5-pyrazolone,
 41. The silver halide developing agent dispersion according to claim 34, wherein the auxiliary developing agent is selected from the group consisting of phenylhydroquinone, 2-hydroxyphenylhydroquinone, phenoxyhydroquinone, 4-methylphenyl-hydroquinone, 1,4-dihydroxynaphthalene, 2-(4-aminophenethyl)-5-bromohydroquinone, 2-(4-aminophenethyl)-5-methylhydroquinone, 4-aminophenethylhydroquinone, 2,5-dimethoxyhydroquinone, 2,5-dibutoxyhydroquinone, m-xylohydroquinone, bromohydroquinone, 3,6-dichlorohydroquinone, 2-dimethylaminomethyltoluhydroquinone, 2-cyclohexylhydroquinone, sec-butylhydroquinone, 2,5-dichlorohydroquinone, 2,5,-diisopropylhydroquinone, 2,5-diiodohydroquinone, 3-chlorotoluhydroquinone, tetrachlorohydroquinone, 2,5-diphenylhydroquinone, 2,5-diresorcylhydroquinone, 2,5-dioctylhydroquinone, dodecylhydroquinone, 4-methoxycatechol, 4-isopropoxycatechol, 3-isopropylcatechol, 4-phenylcatechol, 3,6-dimethylcatechol and 1, 2-dihydroxy-5,8-methano-5,6,7,9-tetrahydronaphthalene.
 42. The silver halide developing agent dispersion according to claim 35, wherein the high boiling solvent has a boiling point above 150*C.
 43. The silver halide developing agent dispersion according to claim 42, wherein the solution of the silver halide developing agent in a high boiling solvent is dispersed in the form of fine colloidal particles.
 44. The silver halide developing agent dispersion according to claim 43, wherein the colloidal particles have a particle size of less than about 1 Mu .
 45. The silver halide developing agent dispersion according to claim 43, wherein the colloidal particles have a particle size of less than about 0.3 Mu .
 46. The silver halide developing agent dispersion according to claim 2, wherein the hydrophilic organic colloid is selected from the group consisting of phthalated gelatin, polyvinyl alcohol, polyvinyl pyrrolidone, polyacrylamide, sodium polyacrylate, polyvinyl-2-methylidazole, acrylamide/1-vinyl-2-methylimidazole copolymers, acrylamide/imidazole copolymers, acrylamide/1-vinyl-2-methylimidazole/acrylic acid copolymers, nitrocarboxymethylcellulose, N-vinylpyrrolidone-acrylic acid copolymers, N-vinylpyrrolidone-acrylic acid-methylacrylate copolymers, vinylphthalimide-acrylic acid copolymers, cellulose acetate hydrogen phthalate, poly-N-methylmethacrylamide, dimethyl-aminoethylmethacrylateacrylic acid copolymers, dimethylamino-ethylmethacrylate-acrylic acid-butyl acrylate copolymers, N,N-diethylacrylamide-acrylamide copolymers, poly-N-methylacrylamide copolymers, N-methylacrylamide-N-hydroxymethylacrylamide copolymers, poly-N-ethylacrylamide, methylvinylketoneacrylamide copolymers and N-vinylpyrrolidone-methacrolein copolymers.
 47. The silver halide developing agent dispersion according to claim 42, wherein the high boiling solvent is selected from the group consisting of phosphoric acid esters, phthalic acid esters, aliphatic dibasic acid esters, aliphatic monobasic acid esters, amides, imides, alcohols, ethers, ketones.
 48. The silver halide developing agent dispersion according to claim 42, wHerein the high boiling solvent is selected from the group consisting of triethyl phosphate, tri-n-butyl phosphate, triphenyl phosphate, tricresyl phosphate, tri-p-tertbutylphenyl phosphate, tri-2-ethylhexyl phosphate, methyl phthalate, ethyl phthalate, n-butyl phthalate, 2-ethylbutyl phthalate, n-propyl phthalate, n-amyl phthalate, isoamyl phthalate, n-octyl phthalate, Beta -methoxyethyl phthalate, ditetrahydrofurfuryl phthalate, ditetrahydrofurfuryladipate, n-octyladipate, 2-ethylhexyladipate, n-hexyladipate, 2-ethylbutyl-acelate, butylsebacate, ditetrahydrofurfurylsuccinate, dibutoxyethylsuccinate, oleic acid butyl ester, oleic acid tetrahydrofurfuryl ester, o-methoxyphenyl acetate, stearic acid butyl ester, triethyl citrate, acetyltriethyl citrate, triethyleneglycol di-2-ethyl hexoate, acetylricinol acid methyl ester, acetylricinol acid methoxyethyl ester, Alpha -acetoxy-butylacetyl succinate, tetrahydrofurfuryl benzoate, diethyl lauryl aminde, dibutyl lauryl amide, tetraethyl phthalamide, N-n-butyl acetanilide, N-methyl-p-methyl acetanilide, N-n-amyl succinimide, N-n-amyl phthalimide, lauloyl piperidine, 4-methyl-2-pentanol, furfuryl alcohol, methyl isobutyl carbinol, 2,4,-di-n-amyl phenol, and the like; ethers such as ethyleneglycol monobenzyl ether; and ketones such as ethyl-N, N-di-n-butylcarbamate, 2-methyl cyclohexanone, 3-methyl cyclohexanone and 4-methyl cyclohexanone.
 49. The silver halide developing agent dispersion according to claim 2, wherein the ratio of the silver halide developing agent to the hydrophilic organic colloid is in the range of about 2:1 to 1:2.
 50. The silver halide developing agent dispersion according to claim 42, wherein the high boiling solvent is capable of easily dissolving the silver halide developing agent and is substantially water-insoluble.
 51. The silver halide developing agent dispersion according to claim 50, wherein the solution of the silver halide developing agent further contains an oleophilic polymer.
 52. The silver halide developing agent dispersion according to claim 51, wherein the oleophilic polymer is selected from the group consisting of polyvinyl acetate, polyvinyl butyral, polyvinyl chloride, polyvinyl propionate, polymethyl acrylate, polyethyl acrylate, polybutyl acrylate, polypropyl acrylate, polymethylmethacrylate, polyethylmethacrylate, polybutylmethacrylate and polypropylmethacrylate.
 53. The silver halide developing agent dispersion according to claim 51, wherein the dispersion further contains a viscosity increasing agent.
 54. The silver halide developing agent dispersion according to claim 53, wherein the viscosity increasing agent is selected from the group consisting of polyacrylamide, cellulose nitrate, and poly-p-sulfostyrene potassium salt. 